CA2043715A1 - Imidazonaphthyridine derivatives - Google Patents
Imidazonaphthyridine derivativesInfo
- Publication number
- CA2043715A1 CA2043715A1 CA2043715A CA2043715A CA2043715A1 CA 2043715 A1 CA2043715 A1 CA 2043715A1 CA 2043715 A CA2043715 A CA 2043715A CA 2043715 A CA2043715 A CA 2043715A CA 2043715 A1 CA2043715 A1 CA 2043715A1
- Authority
- CA
- Canada
- Prior art keywords
- lower alkyl
- substituted
- represents hydrogen
- hydroxy
- aryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Luminescent Compositions (AREA)
Abstract
Disclosed are imidazonaphthyridine derivatives represented by formula (I) (I) wherein:
R1 represents lower alkyl or substituted or unsubsti-tuted aryl; and X-Y-Z represents or wherein R2 represents hydrogen, lower alkyl, alkeny1, aralkeny1, or -C(R5)H-(CH2)n-R4 (wherein R4 represents substituted or unsubstituted aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted furyl, hydroxy-substituted lower alkyl, lower alkanoyloxy, morpholino, lower alkanoyl, carboxy, lower alkoxycarbonyl, cycloalkyl, hydroxy, lower alkoxy, halogen or NR6R7 wherein R6 and R7 independently represents hydrogen or lower alkyl; R5 represents hydrogen, lower alkyl, or phenyl; and n represents an integer of 0 to 3); and R3 represents hydrogen, mercapto, hydroxy, lower alkyl, or aryl and pharmaceutically acceptable salts thereof.
The compounds show a potent anti-inflammatory, anti-allergic and broncho-dilative activity.
R1 represents lower alkyl or substituted or unsubsti-tuted aryl; and X-Y-Z represents or wherein R2 represents hydrogen, lower alkyl, alkeny1, aralkeny1, or -C(R5)H-(CH2)n-R4 (wherein R4 represents substituted or unsubstituted aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted furyl, hydroxy-substituted lower alkyl, lower alkanoyloxy, morpholino, lower alkanoyl, carboxy, lower alkoxycarbonyl, cycloalkyl, hydroxy, lower alkoxy, halogen or NR6R7 wherein R6 and R7 independently represents hydrogen or lower alkyl; R5 represents hydrogen, lower alkyl, or phenyl; and n represents an integer of 0 to 3); and R3 represents hydrogen, mercapto, hydroxy, lower alkyl, or aryl and pharmaceutically acceptable salts thereof.
The compounds show a potent anti-inflammatory, anti-allergic and broncho-dilative activity.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP143460/90 | 1990-06-01 | ||
| JP14346090 | 1990-06-01 | ||
| JP334657/90 | 1990-11-30 | ||
| JP33465790 | 1990-11-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2043715A1 true CA2043715A1 (en) | 1991-12-02 |
| CA2043715C CA2043715C (en) | 1997-01-07 |
Family
ID=26475184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002043715A Expired - Fee Related CA2043715C (en) | 1990-06-01 | 1991-05-31 | Imidazonaphthyridine derivatives |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US5364859A (en) |
| EP (1) | EP0459505B1 (en) |
| JP (1) | JP3016905B2 (en) |
| AT (1) | ATE143661T1 (en) |
| CA (1) | CA2043715C (en) |
| DE (1) | DE69122427T2 (en) |
| DK (1) | DK0459505T3 (en) |
| ES (1) | ES2094772T3 (en) |
| GR (1) | GR3021971T3 (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3016905B2 (en) * | 1990-06-01 | 2000-03-06 | 協和醗酵工業株式会社 | Imidazonaphthyridine derivative |
| US5281610A (en) * | 1991-07-31 | 1994-01-25 | Kyowa Hakko Kogyo Co., Ltd. | Condensed naphthyridine derivatives |
| JPH05194515A (en) * | 1991-07-31 | 1993-08-03 | Kyowa Hakko Kogyo Co Ltd | Condensed naphthyridine derivative |
| US5484924A (en) * | 1991-11-25 | 1996-01-16 | Kyowa Hakko Kogyo Co., Ltd. | Imidazonaphthyridine derivatives |
| WO1994002481A1 (en) * | 1992-07-20 | 1994-02-03 | Kyowa Hakko Kogyo Co., Ltd. | Imidazonaphthyridine derivative |
| US6365231B2 (en) | 1998-06-26 | 2002-04-02 | Kabushiki Kaisha Toshiba | Ammonium halide eliminator, chemical vapor deposition system and chemical vapor deposition process |
| JP2000119271A (en) | 1998-08-12 | 2000-04-25 | Hokuriku Seiyaku Co Ltd | 1h-imidazopyridine derivative |
| SI1212089T1 (en) | 1999-08-21 | 2006-08-31 | Altana Pharma Ag | Synergistic combination of roflumilast and salmeterol |
| US6949247B2 (en) | 2000-12-28 | 2005-09-27 | Unilever Home & Personal Care Usa Division Of Conopco, Inc. | Stable skin care compositions containing a retinoid and a retinoid booster system |
| US20040146561A1 (en) | 2001-05-23 | 2004-07-29 | Naoki Sakurai | Compositions for promoting healing of bone fracture |
| EP1389467B1 (en) | 2001-05-23 | 2013-07-03 | Mitsubishi Tanabe Pharma Corporation | Therapeutic composition for the regenerative treatment of cartilage diseases |
| US7087631B2 (en) * | 2002-07-18 | 2006-08-08 | Inotek Pharmaceuticals Corporation | Aryltetrazole compounds, and compositions thereof |
| JP2006522151A (en) | 2003-04-01 | 2006-09-28 | アプライド リサーチ システムズ エーアールエス ホールディング ナームロゼ フェンノートシャップ | Phosphodiesterase inhibitors in infertility |
| CN101268073B (en) | 2005-09-15 | 2011-10-19 | Aska制药株式会社 | Heterocyclic compound, and production process and use thereof |
| JP2012512246A (en) | 2008-12-17 | 2012-05-31 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | C-ring modified tricyclic benzonaphthyridinone protein kinase inhibitors and uses thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RO66801A (en) * | 1973-05-25 | 1979-08-15 | Lepetit Spa | PROCESS FOR OBTAINING TRIAZOLOIZOQUINOLINE DERIVATIVES |
| US4059584A (en) * | 1974-08-07 | 1977-11-22 | Pfizer | 2-Acylamino-3-[3-(dialkylamino)propyl]imidazo[4,5-b]pyridines |
| ZA848968B (en) * | 1983-11-18 | 1986-06-25 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinolines and 1h-imidazo(4,5-c)quinolin-4-amines |
| IL73534A (en) * | 1983-11-18 | 1990-12-23 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinoline-4-amines,their preparation and pharmaceutical compositions containing certain such compounds |
| CA1271477A (en) * | 1983-11-18 | 1990-07-10 | John F. Gerster | 1h-imidazo[4,5-c]quinolin-4-amines |
| US4760073A (en) * | 1986-04-11 | 1988-07-26 | Schering Corporation | Aryl-substituted naphthyridine and pyridopyrazine derivatives, useful as anti-allergic agents |
| EP0362299A1 (en) * | 1987-07-22 | 1990-04-11 | Schering Corporation | Bicyclic compounds, their use as pharmaceuticals, their preparation, and intermediates useful in their preparation |
| JP3016905B2 (en) * | 1990-06-01 | 2000-03-06 | 協和醗酵工業株式会社 | Imidazonaphthyridine derivative |
-
1991
- 1991-05-31 JP JP3129651A patent/JP3016905B2/en not_active Expired - Fee Related
- 1991-05-31 DK DK91108908.4T patent/DK0459505T3/en active
- 1991-05-31 CA CA002043715A patent/CA2043715C/en not_active Expired - Fee Related
- 1991-05-31 DE DE69122427T patent/DE69122427T2/en not_active Expired - Fee Related
- 1991-05-31 AT AT91108908T patent/ATE143661T1/en not_active IP Right Cessation
- 1991-05-31 ES ES91108908T patent/ES2094772T3/en not_active Expired - Lifetime
- 1991-05-31 EP EP91108908A patent/EP0459505B1/en not_active Expired - Lifetime
-
1992
- 1992-12-29 US US07/999,658 patent/US5364859A/en not_active Expired - Fee Related
-
1994
- 1994-05-12 US US08/241,631 patent/US5468756A/en not_active Expired - Fee Related
-
1995
- 1995-09-11 US US08/526,323 patent/US5536730A/en not_active Expired - Fee Related
-
1996
- 1996-12-11 GR GR960403401T patent/GR3021971T3/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0459505A1 (en) | 1991-12-04 |
| US5468756A (en) | 1995-11-21 |
| DK0459505T3 (en) | 1996-11-18 |
| EP0459505B1 (en) | 1996-10-02 |
| US5364859A (en) | 1994-11-15 |
| US5536730A (en) | 1996-07-16 |
| DE69122427T2 (en) | 1997-03-06 |
| ES2094772T3 (en) | 1997-02-01 |
| JP3016905B2 (en) | 2000-03-06 |
| GR3021971T3 (en) | 1997-03-31 |
| ATE143661T1 (en) | 1996-10-15 |
| CA2043715C (en) | 1997-01-07 |
| DE69122427D1 (en) | 1996-11-07 |
| JPH04226985A (en) | 1992-08-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |